Dyeing process



Patented July 23, 1935 UNITED STATES PATENT OFFICE DYEING PROCESS a N Drawing. Application January 20, 1933, Serial 10 Claims.

This invention relates to an improved dyeing process whereby claret dyeings on the fibre. of excellent fastness to kier-boiling and chlorine are obtained.

According to the invention we combine on the fibre an arylamide of 2:3-hydroxynaphthoic acid, devoid of sulphoni c, carboxylic, or other water-solubilizing groups, with the tetrazo com pound of a diamine obtained by condensing two molecular proportions of a primary o-alkoxyarylamine of the general formula HzN (where R stands for alkyl, and X for hydrogen alkyl, chlorine or bromine), with one molecular proportion of an aromatic aldehyde, for example, benzaldehyde, both arylamine and the aromatic aldehyde being devoid of nitro groups and watersolubilizing groups.

Claret or purple shades of excellent fastness to kier-boiling (cf. Rowe, Journal of the Society of Dyers and Colourists, Feb., 1931, page 33) and chlorine are obtained. The light fastness also is good.

The diamines whichare tetrazotized and used in accordance with the invention are new compounds. We mention the following as exemplifying them, but the invention is not restricted to the use of the diamines here specified.

(1) 4:4 Diamino 2:2 dimethyl :5 di methoxytriphenylmethane.

This can be prepared as follows. 347 parts of the hydrochloride of 3-amino-4-cresol methyl ether (common cresidine) are added to 200 parts of water and the temperature is raised to 50 C. 106 parts of benzaldehyde are then stirred in and the mixture is then stirred for about 20 hours at 95 C. A small amount of hydrochloric acid is added until a distinct mineral acid reaction to Congo paper is shown and unchanged benzaldehyde is removed by steam distillation. The residue is then made alkaline with caustic soda liquor and again steam distilled to remove any un- In Great Britain January 29,

methane.

(5) 2' -Chloro -4 4' -diaminotriphenylmethane.

(6) 2"'-Chloro-2:2'-dimethyl-3:3'- dimethoxy- 4:4'-diamino-triphenylmethane, m. p. 225-6 C.

(7) 2:2 Dichloro-4:4'-diamino-5:5'-dimethoxytriphenylmethane.

(8) 2:2 Dibromo -4:4-diamino-5:5-dimethoxytriphenylmethane.

All the above are readily soluble in dilute acids. They are obtained by condensation of the appropriate aldehyde and amine in presence of hydrochloric acid as described in Example (1) above.

The followingillustrative example describes how the invention is carried into efiect.

4 gms. of the a-naphthylamide of 2:3-hydroxynaphthoic acid are pasted with 9 gms. of Turkey red oil and 16 gms. of caustic soda 76 Tw. The paste is dissolved in 150 cc. boiling water and the solution made up to 1 litre. Cotton yarn is steeped in this solution for half an hour at 35 C., the ratio of volume of solution to weight of cotton being 20:1. The cotton is wrung but not rinsed and then steeped for 30 minutes in a diazo solu tion made up as follows:-2.28 parts of 4:4'-diamino-2 2' dimethyl 5 5 dimethoxytriphenylmethane are dissolved in 40 parts of water and 3 parts hydrochloric acid 32 Tw. The solution is cooled to 10 and diazotized by addition of 3.8 parts of 20% sodium nitrite. It is neutralized with sodium acetate and made up to 500 cc. A second solution is made up containing 'parts salt and 0.5 part acetic acid 50% in 500 parts water. Equal parts of these two solutions are mixed and 200 parts of the mixture used for each 10 gms. of cotton yarn.

then

The dyed cotton is treated by boiling for a short time with a soap solution containing a small quantity of soda ash. The shade is a brightclaret.

Further examples are given in the following table:

Base tetrazotized Coupling component Shade 4:4 Diamino-2:2-dimethyl- 2:3-Hydroxynaphthoic 4- Claret.

5:5-dimetl1oxytriphenylbromo-o-anisidide. methane.

D 2:3-Hydroxynaphtho1c Do.

anilide. I 2:3-Hydroxynaphthoic 4- Do.

bromo-o-anisidide. 2:3-Hydroxynaphthoic 5- Do.

chIOroo-toluidide. 2:3-Hydroxynaphthoic a- Do.

naphthylamide. 2:3-Hydroxynaphthoic p- Do.

anisidide. 2:3-Hydroxynaphthoic 3- Do.

naphthylamide. 2:3-Hydroxynaphtl1oio 0- Do.

anisidide. 3:3:3"-Trirnethoxy-4:4-dl- 2:3-Hydroxynaphtho1c Do.

aminotriphenylmethane. anilide.

Do 2z3-Hydroxynaphthoic p- Do.

onisidide. Do 2:3-Bydroxynaphtho1c 8- Do.

naphthylamide. Do 2:3-Hydroxynaphth0ic oz- Do. naphthylarnicle. Do 2:3-Hydroxynuphth0ic 5- D0.

chloro-o-toluidide. Do 2:3-Hydroxynaphthoic 4 Do.

bromo-o-anisidide. 2:2 Dimethyl 3:313 tn 2:3-Hydroxynaphthoic an- Do.

methoxy 4:4 (liaminoilide. triphenylmethane.

Do 2:3Hydroxynaphth0ic 6- Do.

naphthylamidc. Do 2:3-Hydroxynaphthoic 1) Do.

anisidide. 2:3-Hydroxynr1phthoic 4- Do.

brorno-oanisidide. 2:3-Hydroxynaphthoic 5 Do.

chloro-o-toluidide. :3-Hydroxynaphtholc or Do, naphthylamidc. 3:3'-D Y- :3-Hydroxynaphthoic 2111- Do.

no-triphenylmethane. ilide.

Do 2z3-Hydroxynaphthoic p- Do.

anisidide. D0 :3-Hydroxynaphthoic 4- Do.

brorno-o-anisidide. Do :3-Hydroxynapl1thoic 5- Do.

naphthylamide. D0 :3-Hydroxynaphthoic a- Do.

naphthylamidc. D0 :3-Hydroxynaphth0ic 5- Do. U chloro-o-toluidide. 2 Q dlmethyb :3-Hyclroxynaphthoican- D0.

5:5; dimethoxy 4:4 di- Hide, ammo-triphenylmetbane.

Do :3-Hydroxynaphthoic p- Do.

anisidide. :3-Hydroxynaphthoic 4- D0.

brorno-o-anisidide. :3-Hyldgoxlynapihthoic a- Do. nan t y ami e. 'G Q YI- :3-Hydroxynaphthoic ,3- Do.

313 dunethoxy 4:4 dlnaphthylamide, amlnotriphenylmethane.

D0 :3-Hydroxynaphthoic 5- Do.

chloro-o-toluidide.

All the above have excellent fastness to chlorine and kier boiling.

We claim:

1. A process for the production of fast shades "on textile materials which comprises coupling on the fiber an arylamide of 2-3-hydroxy-naphthoic acid free from water-solubilizing groups with a two molecular proportions of a primary O-alkoxyarylamine of the benzene series, having one of the group, hydrogen, alkyl, chlorine, bromine in a position meta, to each associated group, with an aromatic aldehyde.

3. A process for the production of fast shades on textile materials which comprises coupling on the fiber an arylamide of 2-3-hydroXy-naphthoic acid having the following general formula:

CONHR wherein R represents an aromatic residue of the benzene or naphthalene series which may have substituted thereon members selected from the class consisting of halogen, alkyl, and alkoxy groups, with a tetrazotized diamine having the following general formula:

wherein R represents an alkyl group, X represents hydrogen, alkyl, chlorine or bromine, and Y represents hydrogen or an alkoxy group.

4. A process for the production of fast shades on textile materials which comprises coupling on the fiber an arylamide of 2-3-hydroxy-naphthoic acid free from water-solubilizing and nitro groups with tetrazotized 4-4'-diamino-5-5-dimethoXy-2-2-dimethyl-triphenyl-methane.

5. A process for the production of fast shades on textile materials which comprises coupling on the fiber 2-3-hydroxy-naphthoic-alpha-naphthylamide and tetrazotized 4-4-diamino-5-5'- dimethoxy-2-2'-dimethyl-triphenyl-methane.

6. Fibers dyed with azo dyes having the following general formula:

wherein R represents the residue of an arylamide of 23-hydroXy-naphthoic acid free from water-solubilizing groups, and R, R1 and R2 represent aromatic residues of the benzene series which may have non-water-solubilizing groups substituted thereon and in which members R and R1 have each an alkoxy group ortho to the azo group.

'7. Fibers dyed with azo dyes having the following gencral formula:

amide of 2-3-hydroxy-naphthoic acid free from water-solubilizing and nitro groups, and R, R1

and R2 represent aromatic residues of the benzene series free from water-solubilizing and nitro groups and in which members R and R1 have each an alkoxy group ortho to the azo group.

CONHR' 8. Fibers dyed with azo dyes having the folwherein R represents the residue of an aryllowing general formula: amide of 2-3-hydroxy-naphthoic acid free from CONHR water-solubilizing and nitro groups.

10. Fibers dyed with an azo dye having the following formula:

wherein R represents an aromatic residue of the benzene or naphthalene series which may have substituted thereon members selected from the class consisting of halogen, alkyl, and alkoxy OONH groups, R represents an alkyl group, X repre- MORDECAI MENDOZA. sents hydrogen, alkyl, chlorine or bromine, and WILFRED ARCHIBALD SEXTON.

Y represents hydrogen or an alkoxy group.

9. Fibers dyed with azo dyes having the following general formula:

CH3 CH3 X R I O H 

